U.S. Pat. No. 2,988,537 discloses the following reaction: ##STR1## wherein X is halogen, M is alkali metal and R.sup.1 and R.sup.3 are alkyl or fluorinated alkyl having up to 18 carbon atoms; R.sup.2 is defined as R.sup.1 but limited to 12 carbon atoms.
U.S. Pat. No. 3,091,643 discloses the following reaction: EQU R.sub.x CO.sub.2 R+MOR.sup. .fwdarw.R.sub.x C(OM)(OR.sup.1)(OR) EQU (R.sub.x).sub.2 C(OM)OR.fwdarw.(R.sub.x).sub.2 CO
wherein R.sub.x is a monovalent polyfluoroperhalocarbyl or .omega.-hydroperfluoroperhalocarbyl radical; R and R.sup.1 are hydrocarbyl having up to eight carbon atoms and M is alkali metal.
U.S. Pat. No. 4,238,416 discloses conversion of fluorinated epoxides, ##STR2## to carbonyl compounds such as R.sub.F C(O)CF.sub.3, R.sub.F C(O)CF.sub.2 R.sub.F and (R.sub.F).sub.2 CFC(O)R.sub.F wherein R.sub.F is perfluoroalkyl or .omega.-hydroperfluoroalkyl and R.sup.1 --R.sup.3 are --R.sub.F or --F.
U.S. Pat. Nos. 3,513,203 and 3,683,027 disclose preparation of polyfluorinated ketones by photochemical combination of liquid C.sub.3 F.sub.6 with oxygen and heating the resulting perfluoropolyethers having acid fluoride end groups.
U.S. Pat. Nos. 4,214,070 and 4,160,780 disclose preparation of ketoperfluorosulfonic acids having the formula R.sub.F.sup.1 CF.sub.2 C(O)CF(R.sub.F)SO.sub.2 H and esters thereof, wherein R.sup.1 F and R.sub.F are --R or C.sub.1-4 perfluoroalkyl, and their use as comonomers.
U.S.S.R. Pat. No. 438,636 discloses compounds having the formula ROCF.sub.2 CF.sub.2 C(O)CF(CF.sub.3)OR, wherein R is a fluorinated aliphatic, alicyclic or aromatic group, which are prepared from perfluoro-.beta.-substituted propionate salts.
U.K. Patent Application No. 2,051,831 discloses the fluoroketone, RSCF.sub.2 CF.sub.2 C(O)CF.sub.2 CF.sub.2 SR, where R is C.sub.1-10 alkyl (embracing R.sup.1 SCF.sub.2 CF.sub.2 Z when Z is --C(O)R.sub.F X.sup.1 and R.sub.F X.sup.1 is --CF.sub.2 CF.sub.2 SR.sup.1) and also discloses acyl fluorides and vinyl ethers having the respective formulas RZ(CF.sub.2).sub.3-5 [OCF(CF.sub.3)CF.sub.2 ].sub.0-5 OCF(CF.sub.3)COF and RZ(CF.sub.2).sub.3-5 [OCF(CF.sub.3)CF.sub.2 ].sub.0-5 OCF.dbd.CF.sub.2 wherein Z is --S-- or --SO.sub.2 -- and R is C.sub.1-10 alkyl.
European Patent Application 41,736 discloses compounds of the formula, Y(CF.sub.2).sub.a (CFR.sub.F).sub.b C(O)R'.sub.F, wherein Y includes --SO.sub.2 R, --SO.sub.2 F, --SO.sub.2 Cl; R is H, alkyl or aryl; a and b are, independently, 0 or integers, and R.sub.F and R'.sub.F are, independently, F, Cl, perfluoroalkyl or fluorochloroalkyl. This formula embraces XCF.sub.2 CFYZ when X is --SO.sub.2 R.sup.1, --SO.sub.2 F or --SO.sub.2 Cl, Y is F or Cl, Z is --C(O)R.sub.F X.sup.1 and R.sub.F X.sup.1 is perfluoroalkyl. An enabling process for preparing the compounds is not provided.
European Patent Applications Nos. 41,736 and 41,737 disclose compounds of the formula Y(CF.sub.2).sub.a (CFR.sub.F).sub.b CFR'.sub.F O[CF(CF.sub.2 X)CF.sub.2 O].sub.n CF(CF.sub.2 X')COF and Y(CF.sub.2).sub.a (CFR.sub.F).sub.b CFR'.sub.F O[CF(CF.sub.2 X)CF.sub.2 O].sub.n CF.dbd.CF.sub.2 where Y is an acid group or a group convertible to an acid group; a and b, individually, are 0 or an integer; R.sub.f and R'.sub.f are each independently selected from F, Cl, perfluoroalkyl and fluorochloroalkyl; X is F, Cl or Br; and X' is Cl or Br. These compounds are prepared from an intermediate for which enablement is not provided. These formulae embrace XCF.sub.2 CFYZ when X is --SO.sub.2 R.sup.1, --SO.sub.2 F or --SO.sub.2 Cl; Y is F or Cl, Z is --CF(R.sub.F X.sup.1)OQ.sub.n CF(CF.sub.3)COF or --CF(R.sub.F X.sup.1)OQ.sub.n CF.dbd.CF.sub.2 and R.sub.F X' is perfluoroalkyl.
Kalenko et al., Zh. Vses. Khim. O-va, Volume 19, No. 6, 707 (1974) [Chem. Abstr., Volume 82, 97627p (1975)], disclose the following reaction: EQU RCF.dbd.CF.sub.2 +R.sup.1 COF.fwdarw.CF.sub.3 CFRC(O)R.sup.1
wherein R is --CF.sub.3, --OCF.sub.3 or --O(CF.sub.2).sub.2 CF and R.sup.1 is --CF.sub.2 OCF.sub.3, --CF.sub.2 CF.sub.2 OCF.sub.3 or (CF.sub.2 CF.sub.2).sub.(1-3) H.
Glazkov et al., Izv. Akad. Nauk SSSR, Ser. Khim, No. 4, page 918 (April 1976), disclose preparation of perfluoroether ketones by heating perfluoroalkylvinyl ethers.
European Patent Application No. 47,945 discloses fluorinated keto sulfonyl fluorides R.sub.F C(O)(CF.sub.2).sub.n SO.sub.2 F wherein R.sub.F is F or C.sub.1-10 perfluoroalkyl and n is 0 or an integer of 1 to 7.